[关键词]
[摘要]
目的 研究拟红紫珠Callicarpa pseudorubella的化学成分及其生物活性。方法 利用多种色谱手段(硅胶、Sephadex LH-20、RP-18反相硅胶柱色谱和半制备型HPLC等)进行分离纯化,运用理化性质结合现代波谱学(紫外、红外、核磁、质谱等)技术进行结构鉴定。采用RSL3诱导的HT22小鼠海马神经元细胞模型铁死亡抑制活性进行筛选。结果 从拟红紫珠中分离得到11个化合物,分别鉴定为(7S,7'R,8R,8'S,9S)-芝麻素-9-O-β-D-葡萄糖苷(1 )、(+)-松脂素-4-O-β-D-葡萄糖苷(2 )、(7R,7'R,7″S,7‴S,8S,8'S,8″S,8‴S)-4″,4‴-二羟基-3,3',3″,3‴,5,5'-六甲氧基-7,9';7',9-二环氧-4,8″;4',8‴-双氧-8,8'-双新木脂素-7″,7‴,9″,9‴-四醇(3 )、(7R,7'R,7″R,7‴S,8S,8'S,8″S,8‴S)-4″,4‴-二羟基-3,3',3″,3‴,5,5'-六甲氧基-7,9';7',9-二环氧-4,8″;4',8‴-双氧-8,8'-双新木脂素-7″,7‴,9″,9‴-四醇(4 )、泡桐素(5 )、4-氧代芝麻素(6 )、芝麻素(7 )、β-谷甾醇(8 )、熊果酸(9 )、3β-羟基豆甾-5烯-7-酮(10 )和3β-羟基豆甾-5,22-二烯-7-酮(11 )。生物活性结果显示,化合物7 、10 和11 对RSL3诱导的HT22细胞铁死亡较模型组有明显的抑制活性,其细胞存活率分别为30.37%、31.93%和36.57%(模型组为23.4%)。结论 化合物1 为新化合物,命名为拟红紫珠苷A。所有化合物均为首次从拟红紫珠中分离得到,且3个化合物显示出潜在的铁死亡抑制活性。
[Key word]
[Abstract]
objective To study the chemical constituents of Callicarpa pseudorubella and their biological activities. Methods The chemical constituents were isolated and purified by silica gel, Sephadex LH-20, RP-18 reversed phase silica gel column chromatography and semi-preparative high performance liquid chromatography (HPLC). Then their structures were elucidated by modern spectroscopic analyses (UV, IR, NMR, and HRESIMS) and physicochemical properties. All isolates were evaluated for their inhibitory effect on RSL3-induced ferroptosis in HT22 mouse hippocampal neuronal cells. Results A total of eleven compounds were isolated from C. pseudorubella and identified as (7S,7ʹR,8R,8ʹS,9S)-sesamin-9-O-β-D-glucopyranoside (1), (+)-pinoresinol-4-O-β-D-glucopyranoside (2), (7R,7'R,7″S,7‴S,8S,8'S,8″S,8‴S)-4″,4‴-dihydroxy-3,3',3″,3‴,5,5'-hexamethoxy-7',9',7',9-diepoxy-4,8″,4',8‴-bisoxy-8,8'-dineolignan-7″,7‴,9″,9‴-tetraol (3), (7R,7'R,7″R,7‴S,8S,8'S,8″S,8‴S)-4″,4‴-dihydroxy-3,3',3″,3‴,5,5'-hexamethoxy-7,9', 7',9-diepoxy-4,8″,4',8‴-bisoxy-8,8'-dineolignan-7″,7‴,9″,9‴-tetraol (4), paulownin (5), 4-oxosesamin (6), sesamin (7), β-sitosterol (8), ursolic acid (9), 3β-hydroxystigmast-5-en-7-one (10), and 3β-hydroxystigmast-5,22-dien-7-one (11). Compared with the model group, compounds 7, 10 and 11 exhibited obvious inhibitory activity on RSL3-induced HT22 cells ferroptosis, with the survival rate of 30.37%, 31.93% and 36.57%, respectively (23.4% in model group). Conclusion Compound 1 is a new compound, named as callicoside A. And all compounds are isolated from C. pseudorubella for the first time. Moreover, compounds 7, 10 and 11 exhibit obvious inhibitory activity against RSL3-induced HT22 cells ferroptosis.
[中图分类号]
R284.1
[基金项目]
国家自然科学基金资助项目(32060100);国家自然科学基金资助项目(32100322);贵州省科技计划项目(黔科合基础-ZK[2021]534,QKHZC[2021]411,QKHZC[2022]019);贵州省科技计划项目(黔科中引地[2022]4015)